Summary
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1.
2-Oxocyclohexanecarboxaldehyde reacts with hydrogen peroxide with formation of a mixture of cyclopentanecarboxylic, pimelic, and adipic acids in proportions that depend on the nature of the solvent and the reaction temperature. The highest yield of pimelic acid is attained at temperatures above 20° in water or aqueous t-butyl alcohol.
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2.
When treated with hydrogen peroxide and then subjected to acid hydrolysis, 2-(methylaminomethylene)-cyclohexanone gives a 50% yield of pure pimelic acid and only traces of cyclopentanecarboxylic and adipic acids.
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Literature cited
L. P. Vinogradova, B. A. Rudenko, and S. I. Zav'yalov, Izv. AN SSSR. Otd. khim. n. 1436 (1962); L. P. Vinogradova and S. I. Zav'yalov, Izv. AN SSSR. Otd. khim. n. 2050 (1961).
G. Payne, J. Organ. Chem.26, 4793 (1961).
Organic Syntheses [Russian translation], Vol. 2, 410 (1949).
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The authors thank B. A. Rudenko for help in carrying out the gas-liquid Chromatographic analysis and T. M. Fadeeva for the determination of infrared and ultraviolet spectra.
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Vinogradova, L.P., Zav'yalov, S.I. β-Dicarbonyl compounds. Russ Chem Bull 12, 781–784 (1963). https://doi.org/10.1007/BF01134724
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DOI: https://doi.org/10.1007/BF01134724